There’s no season quite as cozy as winter when it’s beginning to look a lot like Christmas… especially if you find yourself in Middleburg, Virginia this time of year. The historic downtown district is famous for putting on a festive parade each year. However, visit anytime during this season and you’ll find something to admire, whether it’s the storybook-like Main Street or the enchanting storefronts. So if you’re longing for a dose of small town America this season, you know exactly where you should venture to… the best winter town in Virginia!

Nestled in the heart of Virginia's horse country, the town of Middleburg is one of the most charming and picturesque of our state's small towns. And this is the time of year when it shines brightest.
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The history of this incredible state comes alive during this season. The gentleness of falling snow perfectly frames our charming historic architecture.
Each year's event typically takes place the first weekend in December, and it promises all sorts of merriment and festivities.
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Be sure to check out this year's schedule to find out when you should plan your visit!
The event is filled with all sorts of exciting events, with the parade drawing the biggest crowds. Floats, live music, and even a parade on horseback will make its way down Washington Street.
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The charm of this petite town in Loudoun County is absolutely enhanced by this old-fashioned attraction! On the Friday before the big kick out, you can experience an equally enchanting tree lighting.

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Of course, you could just as easily fall into the spirit of the season by taking a quiet walk through the woods. The land surrounding Middleburg is positively gorgeous, and there's no better way to enjoy it than a gentle hiking trail.
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This tiny town, established in 1787, welcomed early visitors to its town and encouraged hunting in its woods. These gorgeous snow-covered forests have enchanted visitors ever since.
While a dusting of snow definitely brings out the seasonal charm of the region, you'll find that Virginia's very own horse country is just as lovable without snow.
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If you visit in a year that is somewhat warmer, you'll still enjoy the gorgeous landscape of this quaint community. Our many historic farms are particularly stunning!
When you head back to town in the afternoon, you won't want to miss the Spirits of Middleburg event from 3 to 6 p.m. Visitors are invited to stroll downtown and enjoy cider, wine, beer, and food pairings from local vendors.
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This Saturday evening event is so much fun! The fun and seasonal beauty spans from one end of town to the other!
No matter your inspiration for visiting Middleburg this time of year, you'll surely find that there's no town merrier during the holidays.
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For more information on Christmas in Middleburg, the best winter town in Virginia, be sure to follow along on Facebook or visit the official website by clicking here. For related content, you can read about another Virginia small town with a truly enchanting Main Street during the holidays.

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More to Explore

Best Winter Town In Virginia

Nikki Rhoades | October 27, 2019

What other places are the most festive towns in Virginia?

Christmas in the Old Dominion is absolutely infectious – once you’ve visited Middleburg, the winter wonderland town in Virginia, you’ll crave more holly jolly holiday fun. Fortunately for locals and tourists alike, there are enough festive towns to comprise an entire road trip through Virginia. There’s enough holiday cheer here to last from Thanksgiving through the New Year!

What are the best things to do for Christmas in Virginia?

Perhaps the best thing to do at Christmas is to explore your local community or the town you’re staying in. The most festive towns in Virginia play up their historical charm, offering picturesque celebration and casual visits with Santa. Each year, it’s worth building a holiday bucket list – and visiting places like the Virginia Christmas cave.

What kinds of activities can I do in winter in Virginia?

There are a number of incredible places to visit in winter in Virginia, especially if you’re a fan of historic charms and landscapes worthy of the big screen. Consider embarking on a wintertime hike or exploring a historic town… either way, you are in for a world of visual splendor!

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